Startseite Naturwissenschaften The crystal structure of 2,2′-((1E,1′E)-hydrazine-1,2-diylidenebis(methaneylylidene))bis(4-chlorophenol), C14H10Cl2N2O2
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The crystal structure of 2,2′-((1E,1′E)-hydrazine-1,2-diylidenebis(methaneylylidene))bis(4-chlorophenol), C14H10Cl2N2O2

  • Xu Fan , Ke-Xiang Liu , Hong-Yu Zhu , Zhong-Yan Li EMAIL logo und Lin Yuan ORCID logo EMAIL logo
Veröffentlicht/Copyright: 5. Januar 2022

Abstract

C14H10Cl2N2O2, triclinic, P 1 (no. 2), a = 6.165(12) Å, b = 7.192(13) Å, c = 7.829(15) Å, α = 74.97(2)°, β = 81.92(2)°, γ = 79.84(2)°, V = 328.3(11) Å3, Z = 1, R gt (F) = 0.0312, wR ref (F 2) = 0.0859, T = 296(2) K.

CCDC no.: 2107221

The molecular structure is shown in the figure. Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal: Yellow block
Size: 0.41 × 0.38 × 0.33 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.50 mm−1
Diffractometer, scan mode: Bruker APEX-II, φ and ω
θ max, completeness: 25.0°, >99%
N(hkl)measured, N(hkl)unique, R int: 3150, 1160, 0.013
Criterion for I obs, N(hkl)gt: I obs > 2 σ(I obs), 1028
N(param)refined: 92
Programs: Bruker [1], SHELX [2, 3]
Table 2:

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).

Atom x y z U iso*/U eq
C1 0.4596 (3) 0.3200 (2) 0.3872 (2) 0.0407 (4)
C2 0.6783 (3) 0.2419 (2) 0.4198 (2) 0.0445 (4)
C3 0.7262 (3) 0.1472 (3) 0.5905 (2) 0.0510 (4)
H3 0.871152 0.092328 0.611733 0.061*
C4 0.5626 (3) 0.1333 (2) 0.7286 (2) 0.0503 (4)
H4 0.596520 0.070425 0.843404 0.060*
C5 0.3478 (3) 0.2124 (2) 0.6973 (2) 0.0459 (4)
C6 0.2954 (3) 0.3033 (2) 0.5293 (2) 0.0455 (4)
H6 0.149081 0.354310 0.509709 0.055*
C7 0.3993 (3) 0.4212 (2) 0.2121 (2) 0.0446 (4)
H7 0.251233 0.468702 0.196384 0.053*
Cl1 0.14214 (8) 0.19598 (8) 0.87486 (6) 0.0676 (2)
N1 0.5439 (2) 0.4472 (2) 0.07842 (17) 0.0469 (4)
O1 0.8469 (2) 0.2561 (2) 0.28996 (16) 0.0632 (4)
H1 0.798238 0.308576 0.194068 0.095*

Source of materials

5-Chlorosalicylaldehyde (1.56 g, 10 mmol), hydrazine hydrate (0.25 g, 5 mmol) and ethanol (30 mL) were heated and stirred at 353 K for 8 h. Then the solvent was concentrated and filtered. The crude product was recrystallized from ethanol to afford yellow crystals (1.31 g, yield 85%).

Experimental details

All hydrogen atoms were identified in difference Fourier syntheses. The U iso values of the hydrogen atoms of phenolic hydroxyl groups were set to 1.5U eq (C) and the U iso values of all other hydrogen atoms were set to 1.2U eq (C).

Comment

Schiff bases are a class of compounds containing the imino group –C=N–, which have important chemical and biological properties [4, 5]. Schiif bases may have antibacterial, anti-inflammatory, anti-tumor and anti-viral biological activities [6, 7]. Salicylaldehyde Schiff bases are an important class of chemical analysis reagents and organic ligands, and they are widely used in fluorescent probes [8]. We have also reported some Schiff bases of salicylaldehyde [9, 10].

The asymmetric unit of the title structure contains one half of the title molecule (see the figure). It can be clearly seen in the structure that the intra molecular hydrogen bonds are formed between the hydrogen atom of the phenolic hydroxyl group and the nitrogen atom of the imine. The molecule is in the trans configuration at the C(7)–N(1) double bond (1.273(3) Å). The bond angle of N(1)–C(7)–C(1) is 121.57(19)°. The geometric parameters of the title structure are all in the expected ranges [11].


Corresponding authors: Zhong-Yan Li and Lin Yuan, College of Chemistry and Bioengineering, Hunan University of Science and Engineering, Yongzhou, Hunan 425199, P. R. China, E-mail: (Z.-Y. Li) and (L. Yuan)

Funding source: Natural Science Foundation of Hunan Province of China

Award Identifier / Grant number: 2021JJ30291

Funding source: Undergraduate Training Program for Innovation and Entrepreneurship of Hunan Province of China

Award Identifier / Grant number: [2021]197-3585

Funding source: Undergraduate Training Program for Innovation and Entrepreneurship of Hunan University of Science and Engineering

Award Identifier / Grant number: 2021

Funding source: Yongzhou Guiding Science and Technology Plan Project

Award Identifier / Grant number: 2021

Funding source: the Construct Program of Applied Characteristic Discipline in Hunan University of Science and Engineering

Funding source: the Scientific Research Fund of Hunan Provincial Education Department

Award Identifier / Grant number: 21A0518, 21C0691

  1. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: This work was financially supported by Natural Science Foundation of Hunan Province of China (2021JJ30291), the Scientific Research Fund of Hunan Provincial Education Department (21A0518, 21C0691), Undergraduate Training Program for Innovation and Entrepreneurship of Hunan Province of China ([2021]197-3585), Undergraduate Training Program for Innovation and Entrepreneurship of Hunan University of Science and Engineering (2021), Yongzhou Guiding Science and Technology Plan Project (2021), the construct program of applied characteristic discipline in Hunan University of Science and Engineering.

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

References

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Received: 2021-11-15
Accepted: 2021-12-17
Published Online: 2022-01-05
Published in Print: 2022-04-26

© 2021 Xu Fan et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution 4.0 International License.

Artikel in diesem Heft

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of {2,2′-{cyclohexane-1,2-diylbis[(azanylylidene)methylylidene]}bis(2,4-dibromophenolato)-κ4 N,N′,O,O′}copper(II) ─ diethylformamide (1/1), C23H23Br4CuN3O3
  4. The crystal structure of 2-(2-methyl-6-phenyl-4H-pyran-4-ylidene)-1H-indene-1,3(2H)-dione, C21H14O3
  5. Crystal structure of bis((1-methylbenzimidazol-2-yl)methyl)amine, C18H19N5
  6. Crystal structure of (E)-N′-(1-(2-hydroxy-4-methoxyphenyl)ethylidene) isonicotinohydrazide, C15H15N3O3
  7. Crystal structure of 2-((4-phenyl-5-(pyridin-4-yl)-4H-1,2,4-triazol-3-yl)thio)acetonitrile, C15H11N5S
  8. The crystal structure of 2,2′-((1E,1′E)-hydrazine-1,2-diylidenebis(methaneylylidene))bis(4-chlorophenol), C14H10Cl2N2O2
  9. Dichlorido-{2,6-bis(4,5-dihydro-1H-pyrazol-3-yl)pyridine-κ3 N,N′,N″}zinc(II), C11H9C12N5Zn
  10. The crystal structure of dichlorido-(2-((4-phenyl-2H-1,2,3-triazol-2-yl)methyl)pyridine-κ2N,N′)palladium(II), C14H12Cl2N4Pd
  11. The crystal structure of 1-(N1-benzyl-2-methyl-4-nitro-imidazol-5-yl)-4-(prop-2-yn-1-yl) piperazine, C18H21N5O2
  12. Crystal structure of (μ4-(1,2,4,5-tetra(1,2,4-triazol-1-ylmethyl)-benzene-κ4N:N1:N2:N3)disilver(I) diperchlorate
  13. The crystal structure of 1-(2-bromoethane)-4-amine-3,5-dinitropyrazole, C5H6Br1N5O4
  14. Crystal structure of (E)-1-(4-benzyl-3,5-dioxomorpholin-2-ylidene)ethyl acetate, C15H15N1O5
  15. The crystal structure of poly[diaqua-(μ2-1,2,4,5-tetrakis(1,2,4-triazol-1-ylmethyl)-benzene-κ2N:N′)-bis(μ3-terephthalato-κ3O:O′:O′′)dicadmium(II)], C17H15N6O5Cd
  16. Crystal structure of (E)-N′-(1-(5-chloro-2-hydroxyphenyl) ethylidene)thiophene-2-carbohydrazide, C13H11ClN2O2S
  17. The crystal structure of [(2,2′-bipyridine-k2 N,N)-bis(6-phenylpyridine-2-carboxylato-k2 N,O)cobalt(II)]-monohydrate, C36H26N4O5Co
  18. Crystal structure of (E)-N′-(2-chloro-6-hydroxybenzylidene)-3-hydroxybenzo-hydrazide monohydrate, C14H13ClN2O4
  19. Crystal structure of 1,1′-(methylene)bis(pyridin-1-ium) bis(1,2-dicyanoethene-1,2-dithiolato-κ2S:S)nickel(II), C42H30N14Ni2S8
  20. Crystal structure of 1,1′-(1,2-ethanediyl)bis(pyridin-1-ium) bis(1,2-dicyanoethene-1,2-dithiolato-κ2 S:S)nickel(II), C20H14N6NiS4
  21. The crystal structure of 1-methyl-1H-pyrazol-2-ium nitrate, C4H7O3N3
  22. The crystal structure of 4,4′-diselanediylbis(8-(hexyloxy)-3,6-dimethyl-1-(piperidin-1-yl)isoquinoline-7-carbonitrile), C46H60N6O2Se2
  23. The crystal structure of tris(6-methylpyridin-2-yl)phosphine selenide, C18H18N3PSe
  24. The crystal structure of 1,2-bis(2,4-dinitro-1H-imidazol-1-yl)ethane ─ acetone (1/1), C11H12N8O9
  25. Crystal structure of [diaqua[2,2′-(1,2-phenylene)bis(1H-imidazole-4-carboxylato-5-carboxy)-κ4N,N′,O,O′]nickel(II)] tetrahydrate, C16H12N4NiO10·4H2O
  26. The crystal structure of tris(4-methyl-1H-pyrazol-1-yl)methane, C13H16N6
  27. The crystal structure of 5,6-dichloro-2-(quinolin-8-yl)isoindoline-1,3-dione, C17H8Cl2N2O2
  28. Crystal structure of (E)-(2-methoxy-benzylidene)-(4-[1,2,4]triazol-1-yl-phenyl)-amine, C16H14N4O
  29. The crystal structure of (Z)-2-(4-(4-bromophenyl)thiazol-2-yl)-4-(3-hydroxybut-2-enoyl)-5-methyl -1,2-dihydro-3H-pyrazol-3-one – methanol (1/1), C18H18N3O4S
  30. Crystal structure of tetraaqua-tris(nitrato-κ2 O,O′) erbium(III) monohydrate, Er(NO3)3·5H2O, H10ErN3O14
  31. The crystal structure of 1-methyl-2-nitro-1H-imidazole 3-oxide, C4H5N3O3
  32. The crystal structure of 1-methyl-2-nitroimidazole, C4H5N3O2
  33. The crystal structure of 2-carboxyl-4-nitroimidazole monohydrate, C4H5N3O5
  34. Crystal structure of bis[hydrido-hexaphenylcarbodiphosphoran][tetra-trifluoromethyl-(μ-diiodo)-diplatinat]
  35. The crystal structure of poly[μ2-aqua- aqua-(μ3-(E)-2-(4-((2-carbamothioylhydrazineylidene)methyl)phenoxy)acetato-κ3 O:S:S)sodium(I)], C10H14N3O5SNa
  36. The twinned crystal structure of [4,4′-bipyridine]-1,1′-diium hexachloridostannate(IV), C10H10N2SnCl6
  37. The crystal structure of [(2,2′-bipyridine-k2 N,N)-bis(6-phenylpyridine-2-carboxylate-k2 N,O)copper(II)], C34H24N4O4Cu
  38. Crystal structure of trans-1,2-bis(pyridinium-4-yl) ethylene bis(2-carboxy-4-bromobenzoate) – water (1/4), C14H14BrNO6
  39. Crystal structure of poly[diaqua-(μ3-fumarato)-(μ3-maleato)-(μ4-1,2,4,5-tetrakis((1H-1,2,4-triazol-1-yl)methyl)benzene)tetracadmium(II)] dihydrate, C34H32N12O9Cd4
  40. Crystal structure of a second modification of Pachypodol, C18H16O7
  41. Crystal structure of methyl 2-(4-(2-(cyclopentyl-amino)-1-(N-(4-methoxyphenyl)-1-methyl-5-phenyl-1-H-pyrazole-3-carboxamido)-2-oxoethyl)phenyl)acetate, C34H36N4O5
  42. The crystal structure of catena-poly[(m2-4,4′-bipyridine-κ2 N:N)-bis(6-phenylpyridine-2-carboxylato-κ2 N,O) zinc(II)], C34H24N4O4Zn
  43. The crystal structure of hexaquamagnesium(II) (2,4-bis(nitroimino)-6-oxo-1,3,5-triazinane-1,3-diide), C3H15MgN7O12
  44. The crystal structure of 7-Bromo-2-(4-chloro-phenyl)-quinoxaline, C14H9BrClN2
  45. Crystal structure of methyl 4-{[4-(4-cyanobenzamido)phenyl]amino}benzofuro[2,3-d]pyrimidine-6-carboxylate, C26H17N5O4
  46. The crystal structure of (4SR)-7-(3,4-dichlorobenzyl)-4,8,8-trimethyl-7,8-dihydroimidazo[5,1c][1,2,4]triazine-3,6(2H,4H)-dione, C15H16Cl2N4O2
  47. Crystal structure of catena-poly[{μ2-3-carboxy-2,3-bis((4-methylbenzoyl)oxy)propanoato-κ2 O:O′}tris(methanol-κ1 O)lanthanum(III)], C63H63LaO27
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